(2R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 85549-53-7
• Molecular Formula: C₉H₁₆O₇
• Molecular Weight: 236.222

Synonyms:(2R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (2R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 9 articles about (2R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

methyl onate (165875-82-1) → (2R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester (85549-53-7,85549-51-5)

Guidance literature:

With potassium carbonate; In methanol; at -20 ℃; for 1h;

DOI:10.1016/0040-4020(95)00150-7

Reference yield: 60.0%

methanol (67-56-1) + 3-Desoxy-D-lyxo-heptulosansaeure (29873-81-2) → (2R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester (85549-53-7,85549-51-5)

Guidance literature:

With Dowex 50W-X₈ (H⁺); for 2h; Heating;

DOI:10.1021/ja952265x

Reference yield:

methyl (methyl 4,5,7-tri-O-benzyl-3-deoxy-α-D-lyxo-hept-2-ulopyranosid)onate (211935-00-1) → (2R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester (85549-53-7,85549-51-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1016/S0040-4039(98)01045-4

upstream raw materials:

methyl (methyl 5-O-benzyl-3-deoxy-α-D-manno-oct-2-ulopyranosid)onate

methyl onate

methanol

3-Desoxy-D-lyxo-heptulosansaeure

Downstream raw materials:

(4aR,6R,8R,8aR)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic acid methyl ester

{(4aR,6R,8R,8aR)-6-Methoxy-2-phenyl-6-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-acetic acid methyl ester

(2S,3R)-2-[((4aR,6R,8R,8aR)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carbonyl)-amino]-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-butyric acid ethyl ester

(4aR,6R,8R,8aR)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic acid [(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyl]-amide

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